4-((7S)-7-(tert-butyldimethylsilyloxy)-1-methyl-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile

Base Information

• Chemical Name: 4-((7S)-7-(tert-butyldimethylsilyloxy)-1-methyl-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile
• CAS No.: 864361-83-1
• Molecular Formula: C₂₂H₂₉ClN₂O₂Si
• Molecular Weight: 417.023
• Mol file: 864361-83-1.mol

Synonyms:4-((7S)-7-(tert-butyldimethylsilyloxy)-1-methyl-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile

Chemical Property of 4-((7S)-7-(tert-butyldimethylsilyloxy)-1-methyl-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((7S)-7-(tert-butyldimethylsilyloxy)-1-methyl-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile

There total 13 articles about 4-((7S)-7-(tert-butyldimethylsilyloxy)-1-methyl-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 7.0%

4-(2-((2S,3S)-2-Acetyl-3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-2-oxoethyl)-2-chloro-3-methylbenzonitrile (864361-81-9) → 4-((7S)-7-(tert-butyldimethylsilyloxy)-1-methyl-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile (864361-83-1)

Guidance literature:

With piperidine; In tetrahydrofuran; at 100 ℃; for 15h;

DOI:10.1021/jm070312d

Reference yield:

4-((7S)-7-(tert-butyldimethylsilyloxy)-1-hydroxy-1-methyl-3-oxo-hexahydro-1H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile (864361-82-0) → 4-((7S)-7-(tert-butyldimethylsilyloxy)-1-methyl-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile (864361-83-1)

Guidance literature:

4-((7S)-7-(tert-butyldimethylsilyloxy)-1-hydroxy-1-methyl-3-oxo-hexahydro-1H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile; With pyridine; trifluoroacetic acid; In tetrahydrofuran; at 0 - 20 ℃; for 5h;

With water; In tetrahydrofuran;

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 50 ℃; for 3h;

Reference yield:

C18H37NO4Si → 4-((7S)-7-(tert-butyldimethylsilyloxy)-1-methyl-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)-2-chloro-3-methylbenzonitrile (864361-83-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / 4-methyl morpholine N-oxide / tetrapropylammonium perruthenate / acetonitrile; CH₂Cl₂ / 2 h / 20 °C

2: TFA / CH₂Cl₂ / 4 h / 20 °C

3: 220 mg / PyBroP; i-Pr₂NEt / CH₂Cl₂; tetrahydrofuran / 3 h / 20 °C

4: 7 percent / piperidine / tetrahydrofuran / 15 h / 100 °C

With piperidine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jm070312d

upstream raw materials:

4-(2-((2S,3S)-2-Acetyl-3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-2-oxoethyl)-2-chloro-3-methylbenzonitrile

4-amino-2-chloro-3-methyl-benzonitrile

N-(3-chloro-4-cyano-2-methylphenyl)acetamide

diethyl 2-(3-chloro-4-cyano-2-methylphenyl)malonate